The Bet
by ImaginationMore
Summary: James and Kerry make a bet. - I'll probably make chapters based around James and other characters, just review with your suggested pairing and I'll look into it. - Rated M for chapter 2.
1. Chapter 1

"Let's shake on it"

"mhm" replied Kerry

James had just shook on a deal he knew he was most likely going to regret, if his team lost the game of paintball the upcoming night, he'd have to do Kerry's laundry for 2 months. But the reward was just too great, through James' eyes. If his team won the game, Kerry would let him fuck her, whenever he wants for the next 5 days.

And so the game was on

* * *

It was only James and Gabriel left on the paintball field; the rest of his team had been annihilated by bright pink paint, and Gabriel's with bright blue. James was currently kneeling behind a low brick wall, in one of the fake houses that had been built for the battlefield, he decided to retreat to the second floor of the house, where he'd have better view over the street.

He couldn't see Gabriel anywhere, which was frustrating. He decided to take the back exit out of the house and scout over to the girls side, which was probably where Gabriel was hiding. As he left, he turned back for a split second, and saw something move on the stairway he had just come down, and as he turned back again, he saw it was Gabriel, creeping up to where he previously was, she must have seen him when he was looking out the window.

Either way, he had a perfect shot at her from the bottom of the stairwell, so he quickly open fired on her lower back, quickly covering her. He had won the game.

* * *

Kerry looked absolutely mortified when James came out of the arena, spotless, with Gabriel trudging behind him, drenched in paint. James had the biggest shit eating grin Kerry has ever seen, an her eyes shot daggers at him.

Gabriel looked apologetic, but she had no idea what had been at stake.

Kerry was dreading what was to come, but she felt kind of aroused too, but she quickly shut that feeling off, and stomped off to her room, leaving Gabriel confused as to why she was so angry at loosing a paintball game.

* * *

James knew the clock started as soon as he fucked her once, from then, he had five days of sex, whenever he wanted it. It was Thursday, so he figured that he'd wait I'lltomorrow to fuck her the first time, and he knew the perfect chance he'd get, Kerry had combat training as her last lesson of the day on Fridays, and she always showered after it to James' knowledge.

Since he had nothing last lesson on Fridays, he spent most of the 90 minute period listening to music and doing homework, until his alarm went of at 3:55, he then went to Kerry's room, and, quickly unlocking it with a lock pick, slipped inside. He knew its be open, as the bolt was on the inside, and you couldn't bolt it from outside. He the waited another few minutes, before slipping into her wardrobe, and patiently waiting for her among the dresses and T-shirts.

She finally entered, and just as James expected, slid the bolt across and quickly started undressing, when she was down to just her underwear, she went into the bathroom, her ass jiggling appealingly. This was going to be fun.

* * *

If people actually want this to continue, I'll add in another chapter ASAP. Apart from that, I'll be uploading a few more chapters on to "Be Confident" too.

See you in the next chapter!


	2. Chapter 2

**I've been a lurker in this section for an age now, and I recently noticed no one had a consistently updated story on here, or at least smut oriented, so I decided to do my own, I'll try and post a new chapter as soon as I can, and I'm trying to do Last of Us chapters every Wednesday, then Cherub chapters each Thursday/Friday.**

**Again, I usually post at random times, so don't quote me on that. Sometimes I'll have a chapter written for days before uploading it.**

* * *

James finally exposed himself about a minute after he heard the shower turn on, and quickly stripped himself down, before approaching the bathroom cautiously, he quietly slid into the bathroom, where luckily the door wasn't in view of the shower, nor anyone in it.

He slid along the wall, and approaching the door to the shower. He decided to quickly open it and jump in, which is exactly what he did, and Kerry jumped and squealed when she felt another body jump in behind her, and their hands came round to grasp her breasts. She shivered as James whispered in her ear.

"I've come to collect my winnings"

She could feel his hard cock nestled between her ass cheeks, but she turned around to face him. She'd got into this position through a bet and decided to make the most of it, dropping her knees, and stared up at him, her hands around his shaft, teasing him, she slowly worked her hands up and down his dick, smirking up at him.

She decided to put him out of his misery, and let her mouth descend on to his shaft, thinking she could take in his whole cock, then pulling back abruptly when she started gagging on it, she made another attempt, this time slower, and found she could only fit in three fourths of his 9 inches.

She started bobbing up and down, adding her tongue into the mix, making James moan. He could feel himself approaching his climax, slowly but surely, and wondered whether to shoot it down her throat or plaster her face, or if she'd object to either, but after all, he'd won the bet he was going to make the most of it.

He decided to let her do what she wanted, and warned her.

"I'm going to-"

"Mmmmmhhhhhmmmm" she hummed, right onto his cock, making him go wild, shooting his load down he throat spurt after spurt. She gulped it down, then let his softening penis fall out of her mouth, standing up to be level with him.

* * *

They just lazily made out for a few minutes, before Kerry let James "clean" her, him spending just a little too much time on her breast, not that she minded at all. After they'd got out and dried themselves, James went to lay on the bed as Kerry dried her hair, when she left the bathroom, she found herself looking straight at his I once again hard cock, and felt an animalistic urge to impale herself on it. She was shocked, and tried reasoning with herself.

"You don't actually want to do this, the only reason you're doing this is because of a stupid bet"

Her more composed side lost, and se found herself practically jumping him, just sliding herself down onto his dick, to James' surprise, she felt her hymen brake, but she'd heard continuing to fuck reduced the pain, and that's exactly what she did, bouncing up and down on his shaft, panting wildly, moaning softly.

Then there was a knock at the door.

* * *

**Who do you want to see on the other side of that door? Tell me in a review, the next chapter will be up**

**ASAP!**


	3. Chapter 3

**I redid this so many times whilst writing it, hope you enjoy.**

**Thanks to all those who reviewed, Bethany easily won.**

* * *

Luckily for the both of them, Kerry had slit the bolt over when she had got back to the room, so although all Cherub agents could unlock it with some effort, not many people had actually done it, and likewise it was frowned upon.

They were frozen mid-thrust, and James finally pulled out of Kerry, an they James quietly snuck into the bathroom an pulled his clothes back on, and when he returned out of the bathroom, Kerry was trying to make herself look like she ITALIC hadn't just had sex.

James turned to leave, cheekily grinning at her and mouthing "I'll be back for more". He approached the door to leave, and shouted back "I'll bring the pictures to stick on tomorrow" to make it seem like they had just been doing homework together.

He was surprised to see Bethany on the other side, Lauren's bitchy friend, also known as "The Cow". She didn't actually look like a cow, and James thought she had some nice bread for her age, and an ass that bounced with her every step, like it was constantly happy. Other than that she had looks that could kill, her slightly puffy lips, with a face that had but a single spot adorning it, which was actually kind of cute.

She looked pissed right now though, and she scowled at him, like usual, and said to him "Only took you half an hour to answer the door there idiot" she tutted at him before pushing past him and walking into Kerry's room, leaving him stood out in the corridor as she slammed the door behind her.

Once he got back to his room, he decided he should actually do some homework, and stuck on headphones and battled through a half hour of Geography homework, which felt more like 2 hours, before he finally finished.

He then heard a knock at his door, and went to open it, to see Bethany smiling smugly. He decided he would not like what she was going to say, but obliged anyway when she asked if she could come in. She went and sat on the side of the bed, before telling him "Kerry told me everything". He instantly froze in place, and slowly turned around to meet her eyes.

"Whatever you do, don't tell anyone I had sex with her" he pleaded

"She didn't tell me shit, but I suspected something was up, and I was right, don't worry, I won't tell anyone, but you've got to do one thing for me"

James was pissed at himself for falling for the oldest trick on the book, but reluctantly replied "What?"

She approached him, placing both her palms on his chest, and whispering "Fuck me"

* * *

James' didn't had much time to merely consider his answer before Bethany thrust her tongue into his mouth, he opened his mouth instinctively. He was taken aback by this sudden act, but it was no less than welcome as their tongues fought lazily.

James decided that Bethany wouldn't take no for an answer too well, so he might as well make the most of it. It wasn't like he didn't want to do it, he was all too eager, just the idea of it being forced kind of putting a dampener on the whole thing.

He slowly lowered Bethany back onto the bed behind her, pulling back from her lips slowly, he slowly undid the buttons on her blouse, and she slipped it off as his hands found their way behind her back, to undo her bra.

She discarded it onto the floor, and let out a surprised moan and James mouth found her left nipple. She not her lip seductively and pulled at the hem of his shirt, and he quickly pulled away and slipped it off, before returning his mouth to her breasts once again, only this time latching on to her right nipple.

She writhed in pleasure as James slid his hand up her thigh, the skirt not offering much defence against his advances, but to Bethany that was a good thing.

He stroked his thumb up and down her slit through the fabric. Bethany was loosing it from all the teasing at this point, ad shimmied out of her skirt and underwear, leaving her completely naked sprawled on the bed in front of him.

He knelt down front of her, and extended his tongue to her wetness, using his thumb to softly stroke her clit as he delved his tongue inside her again and again.

James didn't mind eating girls out, and didn't really see why other guys sometimes refused, they were fine with girls blowing them, but found having it the other way around. Plus, he knew he was good at it, living proof being the girl currently writhing with pleasure on his bed on his bed.

She reached out and tangled her hands in his hair, pulled him further towards her a she approached her climax. Luckily she wasn't a screamer, and just let out a small whimper as the sensations overwhelmed her.

She slowly came down from her climax, her breathing slowly returning to normal. She got up from the bed, only to sink down to her knees in front of him, she slowly unzipped his fly, and then rugged his jeans down to and off of his ankles.

James pulled his t-shirt, and threw it on top of his jeans, Bethany cupped his erection through his boxers and he groaned appreciatively. She smiled up at him seductively, before proceeding to pull down his boxers, taking his socks off with them.

She stared in awe at his raging erection, and even if it was fake, what guy didn't like seeing that?

She slowly pumped her fist up and down his shaft, before extending her tongue to the tip of it, swirling it around of him.

She finally decided it was time to put him out of his misery, and enveloped what she could of his cock. Anything that wasn't covered by her mouth she'd use her hand on, and started humming, sending lovely vibrations down his stiff rod.

She'd read somewhere that it was almost impossible to gag whilst humming, and gave this information a try as she crammed as much cock as she could down her throat, and it seemed like this was true, as it was almost easy to do.

James on the other hand was close to coming from her depth throating him, and gently prised her head from his cock. She got the message and stood before him, but was shocked when he abruptly picked her up, and shoved her against the back wall, one hand holding her ass up, the other one supporting himself.

She lifted her legs instinctively, and wrapped them around his back. She let out a stifled moan as he entered her, loving every second of it. Once he was buried the hilt inside of her, he slowly pulled back, before quickly slamming back into her, pounding he against the wall, her breasts bouncing in time with each thrust.

James suddenly realised he hadn't asked a very important question, but without missing a beat, asked her "Are you on the pill?"

She nodded wildly, and James took that both as her saying yes, and asking him to go faster. He took her advice, and increased his speed as he impaled her tight pussy on him again and again.

They both reached their climax's at roughly the same time, her walls convulsing on him as he shot his seed deep within her. James, now feeling a lot weaker without the constant adrenaline collapsed on the bed, Bethany laying on top of him.

* * *

**I didn't like this bit so I redid it, - go to chapter 4.**

* * *

**Lost inspiration quite a few times whilst writing this chapter, so I might not put up another till next Thursday, and on top of that, I need to update my TLOU story.**

**Who do you want to see in the next chapter?**


	4. Chapter 4 - Lauren

**Enjoy...**

* * *

Lauren knocked on James' door, and recoiled slightly when she heard moans coming from inside, and went straight back to her room. She should probably warn James having underage sex with a girl in your room, who was extremely loud, was a surefire way to get kicked out of the room, but she doubted she'd be able to fit it into a conversation without it being too awkward, instead, she stripped herself

She always found James attractive, and wanted nothing more for him to push her against a wall and fuck her till she couldn't walk, but she knew it was wrong, even if it was her strongest fantasy, and no matter how hard she tried, it always came to mind when she was pleasuring herself.

She was frustrated that she couldn't do anything with him since he was her brother, which is why she had to stuck to pleasuring herself with only her imagination for material. After she'd came, she always felt a distinct sense of disgust for herself, because she knew it was wrong.

She decided she had to do something. This was getting too much, and she'd either be rejected or accepted, but it was time to face the truth.

Line

James got a ring on his phone, since it was coming from his mobile, he knew it wasn't a member of staff, as they'd call his room phone. He got up from the chair, his knees aching slightly from sitting down for too long, and stumbled over to his dock and quickly checked the display before answering.

"Hey Lauren"

"Hey James, I wondered if you could come round to my room if you get a spare moment? I've got some homework on factorising quadratics and I've got no clue even when to start"

This was a complete lie, she could do all of it pretty easily, but she knew James was good at maths, and wouldn't mind spending a few minutes "helping" her out.

"Yeah, sure. I'll be up in a min"

Lauren rubbed her legs together in excitement, but she was secretly extremely nervous that he'd refuse her, and worse yet, tell someone about it.

She lost herself just thinking about the endless things that could go wrong, but a knock at the door drew her back to her senses, and she went to the door, and let James in.

She led him over to her desk, and he took a seat on one of the desk chairs, Lauren resting herself on the other one. Lauren made it seem like she was legitimately stuck, and James tried explaining it to her well, trying to keep his glance away from the amount of cleavage she was exposing in that extremely low cut top.

Lauren caught him looking, and turned back toward the work as she blushed, and tried a few questions before "accidentally" dropping her pen to the side of her chair. She'd planed this, and was wearing a skirt that would show her whole ass if she bent over too much, and that's exactly what she did, leaning of te edge of her chair, giving James a perfect view of her tight little ass.

James wanted to break all his morals and just fuck her at that point, he wanted to stand up, pull down her panties, and fuck her until she couldn't walk, which Lauren probably wouldn't mind, but he didn't know that.

She didn't really know what response she was expecting exactly, but she needed to advance things a bit.

And she knew exactly how.

* * *

**Small chapter, but I'll be posting part 2 of this either Friday or Saturday (hopefully) with the follow up, which contains a lemon.**


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